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I Got Stealthed

I met Dave at the bars. We hit it off immediately and spent the night talking, until the bar finally shut down. We left and decided to go to a new bathhouse that had just opened down the street. We got checked in and got a shared room. We stripped off, making out briefly, and then went out to explore. We got in the hot tub for a bit and chatted with some guys. Had a nice chat but decided to get out and roam a bit more. The club was nice but plain so we headed back to the room where we made out,

JamieLong

JamieLong in BB

First Time Bb Bottoming

I hadn't seen Jack in several months. We used to hang out at clubs, but never did anything beyond making out. Apparently he had moved out of the city, but was back visiting family and friends. We had a couple drinks and caught up. We started talking about the last time we were making out and he asked me if I wanted to do anything. I said of course, so we left the bar and headed for a nearby park. It was after midnight by the time we got there. There were a couple trails that had a reputation for

JamieLong

JamieLong

Denver Trip

I love business trips. All all-expense paid to go fuck guys in another part of the world. This time I was sent to Denver for ten days. The first night I was there I went out to a couple bars, chatted with a few guys but no one really caught my eye. The clubs eventually closed down and I was looking around the parking lot of the last bar I was at, watching my prospects dwindle rapidly, when I saw a cute little twink sitting in his car. He was probably around twenty-two. I walked up to his car and

JamieLong

JamieLong

Sex in Public pt. 3

I met another guy on Grindr while I was out in downtown Portland one night. I don't know what it is, but I went through this period in my late thirties where guys aged 18-22 were thirsty for me. This guy was 20, so he couldn't meet me at a bar, so I went down to Riverplace, on the Willamette river, where his apartment was. I was dressed for going out, and he was in a hoodie and sweats. He was shorter than me, but built like a jock. I had a condom and lube with me, but I usually don't tell people

JamieLong

JamieLong

Sex in Public pt. 2

Turns out I've had sex in public quite a bit. I'll share a couple more here. At my old place out in the suburbs, there was a paved trail that went back behind the houses and along a greenway that ran along the freeway. There was some light coming through from the freeway, but at night, it was quite dark. One night a cute 18 year old twink messaged me from less than 1000 ft away. He was visiting his sister and was looking for some fun in the new city. After chatting a bit, he wanted to meet

JamieLong

JamieLong

Sex in Public pt. 5

Managed another park hookup while I was house-sitting for some friends out in the suburbs last week. I was feeling really horny, but mainly wanted someone to dump a load in my ass. It was getting pretty late and I was getting ready to go to bed when a 26 year old messaged me on Grindr. Turns out he was a guy I had hooked up with before. He always insisted on using a condom with me, but the last time we hooked up, he tried to fuck me bare, but I wasn't cleaned out or feeling it. Tonight I was def

JamieLong

JamieLong

Sex in Public pt. 4

There's park that was by my house in the suburbs that I had jogged by a couple times, but never really went into, and I ended up meeting a 19 year old bottom there one night. We had been chatting on Grindr for a while (he lived less than a mile away) but he was flaky as fuck and never really wanted to meet up. One night as I hit him up he said let's meet up, and told me about the trails that this little park has. I agreed to meet him and put on sweats, no underwear of course, a hoodie, and runni

JamieLong

JamieLong

Boyfriend and I Fucked by Hung Muscle Stud

The first time my cock was ever in a guys ass bareback was only for a few seconds when I was 20. I had gone home with an 18-year-old twink and after we were naked I was lying on this couch and he straddled my cock and lowered himself on to my bare cock. (No lube, it was pretty impressive.) I was, of course, paranoid about STDs so I asked him for a condom. Still ended up being a great fuck but I do regret asking for that condom. The next time was about a year later with the guy who would become m

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JamieLong in Boyfriend

Favorite Hookup Outfit?

Anyone have a favorite hookup outfit? I like a t-shirt or a hoodie, shorts or sweats, no underwear unless I'm bottoming in which case I wear a jock strap, and slip on shoes. I love being able to strip off in a couple seconds and be ready to fuck. I have a sleeveless hoodie that I love wearing when it's nice out; it shows of my arms nicely. I have a couple kilts as well, but I've only hooked up once when I was wearing one. I really want to get fucked while wearing one.

JamieLong

JamieLong

Condom to Bareback

I’ve known my friend Chris for quite a few years. We see each other out at the bars a lot, and we hook up occasionally. He’s usually pretty religious about wearing a condom. One night I saw him on Grindr and hit him up asking if he wanted to meet up. He was hungry so he picked me up and we went to a food cart so he could eat. Afterwards we drove up to a park overlooking the city and parked just outside the locked gate. We made out for a little bit and he sucked me for a while. We got out and wen

JamieLong

JamieLong in BB

Taking My First BB Load

I had already taken a cock bareback, but the guy pulled out before he came. I had been fucked a couple times before that by guys wearing condoms, and it was fine, but it didn't really do much for me. I got off, but it wasn't anything to write home about. The first time a guy actually came in me was the first time I really got the appeal of bottoming. I was 21 at the time and we met on an AOL chat room (late 90s, lol) and I agreed to meet him at his place. He was a fit twink just a little ta

Tricked by a Twink

I had met a cute 18 year old twink at an all ages club and after exchanging a few calls, we finally agreed to meet up at my apartment. I was expecting more of a date, but he had other ideas, which was fine by me, because I really wanted to fuck this little twink. I was mostly topping at the time, and although I had fucked bareback before, I was using condoms pretty regularly. We went out to get food and afterwards came back to my place. He looked around a little bit and started putting the moves

JamieLong

JamieLong in BB

Taking My First Anonymous Bathhouse Load

I went to Steam Portland one night looking to get fucked. I had gone a couple time before looking to bottom, but either struck out or ending up topping. I had cleaned out and lubed up with a dildo at my place before heading out. When I got to Steam it was moderately busy. I went to the steam room for a bit just to hang out, but no one caught my eye. After a bit I got up and made a circuit. I saw someone was at one of the glory holes, so I went up and opened my towel up and put my cock through. A

JamieLong

JamieLong in BB

Public Park Fuck

I messaged a cute 19 year old with a great bubble butt on Grindr one night, and after chatting for about an hour or so, we agreed to meet up. We didn’t specifically mention having sex, but I was pretty sure it was going to happen. We lived kinda far from each other so we arranged to meet up halfway at a park near where he used to go to high school. I got there and I saw him on a path by the baseball diamond, he was even cuter than his pictures. It was a warm night and we were both wearing just s

JamieLong

JamieLong in BB

Giving my first anonymous BB load at a Bathhouse

I had been to several bathhouses before, Club Portland, Steam Portland, but always with someone I knew or was hooking up with that night. I had even fucked bareback at bathhouses, and been fucked bareback, but always with people I went there with. We would either get a room so we could be private or go off into a corner and fuck, and if someone wanted to join I would just wave them off. The first time I went alone I was prepared to use a condom. Steam Portland has them everywhere. I got a r

JamieLong

JamieLong in BB

An Unexpected Breeding

In my early twenties I was quite the slut. I usually topped, and didn't mind if guys wanted to use condoms. I still don't even though I prefer bareback. I met this guy Tony at a bar one night and ended up going back to his place. We made out on his bed for a while, and before we even got our clothes off I could tell he was going to try to fuck me. At that point I wasn't bottoming much, mainly because there were just so many bottoms in town, and also my first experience bottoming wasn't that grea

JamieLong

JamieLong in Breeding

Fuck Buddy FINALLY Breeds Me!

I've known my fuck buddy James for years. We met at a party I had at my downtown apartment. We hit it off, and he ended up being the last one at the party. We were talking in the kitchen as it was the farthest room from the bedroom where my boyfriend had gone to sleep. James and I were both leaning against the counter when we reached the inevitable lull in the conversation. At the same time we both leaned in and started kissing. He's a short Hispanic dude, wiry but muscular frame, and you'd thin

JamieLong

JamieLong in BB

DPed By Married Couple

I had met Evan and Eric through my ex-boyfriend when we were still together and always thought they were really cute. About a year after my breakup I ran into them one snowy day at one of the local gay bars. Snow days are kinda rare, and the city was pretty much shut down. We made it to last call and started walking back home. I made a joke about them stopping at mine to warm up since it was on the way, and to my surprise they agreed. While we were at my place chatting someone brought up sharing

JamieLong

JamieLong in BB

Fucking a Stripper

In Oregon, strippers can be as young as 18 to work in bars. I was watching a cute one one night, he was short, maybe 5’2” maybe 105lbs. He kept making eye contact with me and I tipped him a couple times. At the end of the night as the bar was closing I left and saw him standing out on the street in a t-shirt, short shorts and sandals. “Good show” I told him. “You liked it?” He asked. “Made me wanna take you home,” I replied. “So take me home daddy,” he said coyly. We walked back to my

JamieLong

JamieLong in BB

Teen Cums Hands-free

There used to be an all-ages club in Portland, and from time to time I'd go there after the bars closed to sober up and dance (they had the best music). One Saturday night I ended up there and was dancing for about 30 minutes when this teen started dancing with me. He was really cute and well-built, not too muscular but he was quite fit. We talked for a while and he asked me where I lived. I told him I only lived about a half a mile away and he asked me if I wanted to get out of there. I agreed

JamieLong

JamieLong in BB

Finally Breeding the Ex

MY first dating experience was when I was 19 and I dated this guy Ken for about 3 months before he dumped me for another guy. I don't really count him as a boyfriend since we were only dating a few months, but I still call him my ex. Or first date started in the middle of the night. He picked me up and we drove around, parked for a bit and made out for a while. Then we went back to his place and fooled around. We only kissed and sucked each other, but he was the first guy to actually let me shoo

JamieLong

JamieLong in Breeding

Bred By a Latino Before Work

I work up earlier than usual one morning before work. I was feeling horny so I got on Grindr and spent a while looking for someone to fuck me. I ended up finding a muscular Latino guy with what looked like a big cock about 30 minutes before I had to leave for work., I finished cleaning out and showering and went to his place which was conveniently on the way to my work. He met me at the door wearing sweatpants and a t-shirt. His English wasn't too great, but he led me through to his room. By thi

JamieLong

JamieLong in BB

21-Year-Old Twink Ditches Condoms

I met Adam online and we ended up going out on a date. He was 20 and I was 22 at the time. It went really well and we went back to my place and got naked. He had a beautiful uncut 7 inch cock that I loved to suck. We sixty-nined for a bit and then he rolled a condom onto my cock and rode it until we both came. We met up a half dozen more times, a couple times we sucked each other off, and the other times, I would fuck him, but always with a condom. I didn't see him for while after that. Aft

JamieLong

JamieLong in BB

He Didn't Know He Was Inside Me

Most guys will fuck bareback. Even if they say they don't, they usually will. I hooked up with a guy I had met out at the bars a few times and ended up going over to his place. We kissed for a while on his bed and things started to get hot and heavy. I stripped him and revealed a nice 6 inch cock with a slight upward curve to it. I sucked him off for a bit until he started kissing me again, then took off all my clothes and started going down on me. After sucking me for a bit he started lick

JamieLong

JamieLong in BB

Fucking Undetected

I met Matt on Craigslist, back when they still had the personals section. He advertised as a vers bottom, and when I saw pics of his body and cock I knew I had to meet up with him. He had a massive 8.5" cock. I told him I usually topped at that point, so he was looking forward to hook up as well. He told me he was poz, but undetectable, but I could fuck him bareback if I wanted. I told him I prefer to use a condom (in those days) and he was cool with that and he had some available. He was also i

JamieLong

JamieLong in BB

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